Benzamide compound and use thereof

ABSTRACT

The present disclosure relates to a benzamide compound as shown in Formula I, an insecticidal comprising same, and a use of the compound as an insecticide in the fields of agriculture, forestry and health.

RELATED APPLICATIONS

The present application is a National Phase of International ApplicationNumber PCT/CN2019/085737 filed May 7, 2019 and claims priority toChinese Application Number 201810448081.X filed May 11, 2018.

FIELD OF THE INVENTION

The present invention belongs to the field of agricultural insecticides;and particularly relates to a novel benzamide compound and use thereof.

BACKGROUND OF THE INVENTION

The patent JP2007099761A relates to a benzamide compound havinginsecticidal activity, and specifically discloses the followingstructure: CK1 (compound No. 1-23), CK2 (compound No. 1-24), CK3(compound No. 1-206).

The patent CN102112437A discloses a compound represented by thefollowing Formula and specific compounds CK4 (compound No. 6-18), CK5(compound No. 1-128), CK6 (compound No. 1-163), CK7 (compound No.1-171), CK8 (compound No. 7-130), CK9 (compound No. 7-135), CK10(compound No. 7-169), CK11 (compound No. 7-174), CK12 (compound No.8-111), CK13 (compound No. 8-146), CK14 (compound No. 8-155), havingcertain insecticidal activity:

The patent CN102119144A discloses the following compound CK15 (compoundNo. 3-14), having certain insecticidal activity.

The patent CN102119143A discloses the following compound CK16 (compoundNo. 7-1574); the compound has certain insecticidal activity; moreover,the compound is, as an insecticide, being studied and developed, and itsgeneric name is broflanilide.

While there is no report on the compound shown in the Formula I and itsinsecticidal activity of the present invention in the prior art.Moreover, compared with the prior art, the compound of the presentinvention has higher insecticidal activity and more excellentfast-acting insecticidal efficacy.

SUMMARY OF THE INVENTION

The objective of the present invention is to provide a benzamidecompound. The compound can be used in the preparation of a drug forcontrolling pests in agricultural and other fields.

The technical solution of present invention is as follows:

A benzamide compound, as shown in Formula I:

in the formula:

R₁ and R₂ are each independently selected from H, halogen, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy;

R₃ is selected from heptafluoroisopropyl or nonafluoro-2-butyl;

R₄ and R₅ are each independently selected from H, C₁-C₆ alkyl, C₁-C₆haloalkyl or cyanomethyl; moreover, at least one of R₄ and R₅ isselected from cyanomethyl;

R₆ is selected from H, halogen, cyano, nitryl, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy; C₁-C₆ alkylthio or C₁-C₆haloalkylthio; n=1, 2, 3, 4 or 5; when n is more than 1, R₆ can be thesame or not the same.

X₁, X₂, X₃, and X₄ are each independently selected from H, halogen,cyano or C₁-C₆ alkoxy; moreover, X₁, X₂, X₃, and X₄ are notsimultaneously H.

Preferably, the compound of the present invention is as follows: in theFormula I,

R₁ and R₂ are each independently selected from H, halogen, C₁-C₄ alkyl,C₁-C₄ haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy;

R₃ is selected from heptafluoroisopropyl or nonafluoro-2-butyl;

R₄ and R₅ are each independently selected from H, methyl, ethyl orcyanomethyl; moreover, at least one of R₄ and R₅ is selected fromcyanomethyl;

R₆ is selected from H, halogen, cyano, nitryl, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy; C₁-C₄ alkylthio or C₁-C₄haloalkylthio; n=1, 2, 3, or 4;

X₁ is selected from F;

X₂, X₃, and X₄ are each independently selected from H, F or cyano.

More preferably, the compound of the present invention is as follows: inthe Formula I,

R₁ and R₂ are each independently selected from H, halogen, methyl,ethyl, trifluoromethyl or difluoromethoxy;

R₃ is selected from heptafluoroisopropyl or nonafluoro-2-butyl;

R₄ and R₅ are each independently selected from H, methyl, ethyl orcyanomethyl; moreover, at least one of R₄ and R₅ is selected fromcyanomethyl;

R₆ is selected from H, F, Cl, Br, cyano, nitryl, methyl, ethyl, propyl,tertiary butyl, trifluoromethyl, heptafluoroisopropyl, methoxy ortrifluoromethoxy; n=1, 2 or 3;

X₁ is selected from F;

X₂, X₃, and X₄ are each independently selected from H, or F.

Further preferably, the compound of the present invention is as follows:in the Formula I,

R₁ and R₂ are each independently selected from H, halogen, methyl,ethyl, trifluoromethyl or difluoromethoxy;

R₃ is selected from heptafluoroisopropyl or nonafluoro-2-butyl;

R₄ is selected from cyanomethyl;

R₅ is selected from H, methyl, ethyl or cyanomethyl;

R₆ is selected from H, F, Cl, Br, cyano, nitryl, methyl, ethyl, propyl,tertiary butyl, trifluoromethyl, heptafluoroisopropyl, methoxy ortrifluoromethoxy; n=1, 2 or 3;

X₁ is selected from F;

X₂, X₃, and X₄ are each independently selected from H, or F.

Or, further preferably, the compound of the present invention is asfollows: in the Formula I,

R₁ and R₂ are each independently selected from H, halogen, methyl,ethyl, trifluoromethyl or difluoromethoxy;

R₃ is selected from heptafluoroisopropyl or nonafluoro-2-butyl;

R₄ is selected from H, methyl, or ethyl;

R₅ is selected from cyanomethyl;

R₆ is selected from H, F, Cl, Br, cyano, nitryl, methyl, ethyl, propyl,tertiary butyl, trifluoromethyl, heptafluoroisopropyl, methoxy ortrifluoromethoxy; n=1, 2 or 3;

X₁ is selected from F;

X₂, X₃, and X₄ are each independently selected from H, or F.

In the definition of the compound shown in the Formula I above,generally, the terms used herein represent the following substituents:

Halogen: F, Cl, Br or I.

Alkyl: linear or branched alkyl, such as methyl, ethyl, n-propyl,isopropyl or different butyl, amyl or hexyl isomers.

Haloalkyl: linear or branched alkyl; H atoms on these alkyls may bepartly or totally substituted by halogen, such as chloromethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,

Trifluoromethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl

nonafluoro-2-butyl

1,1,2,2,2-pentafluoroethyl.

Alkoxy: linear or branched alkyl, bond to a structure by an oxygenatomic bond, such as methoxy, ethoxy, tert-butoxy.

Haloalkoxy: H atoms on alkoxy may be partly or totally substituted byhalogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy,fluoromethoxy, difluoromethoxy, trifluoroethoxy, chlorofluoromethoxy,trifluoroethoxy.

Alkylthio: linear or branched alkyl, bond to a structure by a sulphuratomic bond, such as methylthio, ethylthio.

Haloalkylthio: H atoms on alkylthio may be partly or totally substitutedby halogen, such as difluoromethylthio, trifluoroethylthio.

Cyanomethyl: CNCH₂—.

Partial compounds of the Formula I of the present invention are shown intables 1-70, but the present invention is not limited to thesecompounds.

In the Formula I, when R₁═R₂═CH₃, R₃═heptafluoroisopropyl, X₁═F,X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a different substituentas shown in table 1; and the compounds are represented by No. 1.1-1.321.

TABLE 1 No. (R₆)n No. (R₆)n No. (R₆)n 1.1 2-F 1.2 2-Cl 1.3 2-Br 1.4 3-F1.5 3-Cl 1.6 3-Br 1.7 4-F 1.8 4-Cl 1.9 4-Br 1.10 2-I 1.11 2-CN 1.122-NO₂ 1.13 3-I 1.14 3-CN 1.15 3-NO₂ 1.16 4-I 1.17 4-CN 1.18 4-NO₂ 1.192-CH₃ 1.20 2-C₂H₅ 1.21 2-CH₂CH₂CH₃ 1.22 3-CH₃ 1.23 3-C₂H₅ 1.243-CH₂CH₂CH₃ 1.25 4-CH₃ 1.26 4-C₂H₅ 1.27 4-CH₂CH₂CH₃ 1.28 2-CH(CH₃)₂ 1.292-CH₂CH₂CH₂CH₃ 1.30 2-C(CH₃)₃ 1.31 3-CH(CH₃)₂ 1.32 3-CH₂CH₂CH₂CH₃ 1.333-C(CH₃)₃ 1.34 4-CH(CH₃)₂ 1.35 4-CH₂CH₂CH₂CH₃ 1.36 4-C(CH₃)₃ 1.37 2-CF₃1.38 2-CF(CF₃)₂ 1.39 2-OCH₃ 1.40 3-CF₃ 1.41 3-CF(CF₃)₂ 1.42 3-OCH₃ 1.434-CF₃ 1.44 4-CF(CF₃)₂ 1.45 4-OCH₃ 1.46 2-OC₂H₅ 1.47 2-OCF₃ 1.48 2-OCHF₂1.49 3-OC₂H₅ 1.50 3-OCF₃ 1.51 3-OCHF₂ 1.52 4-OC₂H₅ 1.53 4-OCF₃ 1.544-OCHF₂ 1.55 2-OCH₂CF₃ 1.56 2-SCH₃ 1.57 2-SCF₃ 1.58 3-OCH₂CF₃ 1.593-SCH₃ 1.60 3-SCF₃ 1.61 4-OCH₂CF₃ 1.62 4-SCH₃ 1.63 4-SCF₃ 1.64 2,3-2F1.65 2,3-2Cl 1.66 2,3-2Br 1.67 2,4-2F 1.68 2,4-2Cl 1.69 2,4-2Br 1.702,5-2F 1.71 2,5-2Cl 1.72 2,5-2Br 1.73 2,6-2F 1.74 2,6-2Cl 1.75 2,6-2Br1.76 3,4-2F 1.77 3,4-2Cl 1.78 3,4-2Br 1.79 3,5-2F 1.80 3,5-2Cl 1.813,5-2Br 1.82 2,3-2CN 1.83 2,3-2NO₂ 1.84 2,3-2CH₃ 1.85 2,4-2CN 1.862,4-2NO₂ 1.87 2,4-2CH₃ 1.88 2,5-2CN 1.89 2,5-2NO₂ 1.90 2,5-2CH₃ 1.912,6-2CN 1.92 2,6-2NO₂ 1.93 2,6-2CH₃ 1.94 3,4-2CN 1.95 3,4-2NO₂ 1.963,4-2CH₃ 1.97 3,5-2CN 1.98 3,5-2NO₂ 1.99 3,5-2CH₃ 1.100 2,3-2C₂H₅ 1.1012,3-2(CH₂)₂CH₃ 1.102 2,3-2CH(CH₃)₂ 1.103 2,4-2C₂H₅ 1.104 2,4-2(CH₂)₂CH₃1.105 2,4-2CH(CH₃)₂ 1.106 2,5-2C₂H₅ 1.107 2,5-2(CH₂)₂CH₃ 1.1082,5-2CH(CH₃)₂ 1.109 2,6-2C₂H₅ 1.110 2,6-2(CH₂)₂CH₃ 1.111 2,6-2CH(CH₃)₂1.112 3,4-2C₂H₅ 1.113 3,4-2(CH₂)₂CH₃ 1.114 3,4-2CH(CH₃)₂ 1.115 3,5-2C₂H₅1.116 3,5-2(CH₂)₂CH₃ 1.117 3,5-2CH(CH₃)₂ 1.118 2,3-2C(CH₃)₃ 1.1192,3-2CF₃ 1.120 2,3-2OCH₃ 1.121 2,4-2C(CH₃)₃ 1.122 2,4-2CF₃ 1.1232,4-2OCH₃ 1.124 2,5-2C(CH₃)₃ 1.125 2,5-2CF₃ 1.126 2,5-2OCH₃ 1.1272,6-2C(CH₃)₃ 1.128 2,6-2CF₃ 1.129 2,6-2OCH₃ 1.130 3,4-2C(CH₃)₃ 1.1313,4-2CF₃ 1.132 3,4-2OCH₃ 1.133 3,5-2C(CH₃)₃ 1.134 3,5-2CF₃ 1.1353,5-2OCH₃ 1.136 2,3-2OCF₃ 1.137 2,3-2SCH₃ 1.138 2,3-2SCF₃ 1.1392,4-2OCF₃ 1.140 2,4-2SCH₃ 1.141 2,4-2SCF₃ 1.142 2,5-2OCF₃ 1.1432,5-2SCH₃ 1.144 2,5-2SCF₃ 1.145 2,6-2OCF₃ 1.146 2,6-2SCH₃ 1.1472,6-2SCF₃ 1.148 3,4-2OCF₃ 1.149 3,4-2SCH₃ 1.150 3,4-2SCF₃ 1.1513,5-2OCF₃ 1.152 3,5-2SCH₃ 1.153 3,5-2SCF₃ 1.154 2-F-4-Cl 1.155 2-F-4-Br1.156 2-F-4-I 1.157 2-F-3-Cl 1.158 2-F-5-Cl 1.159 2-F-6-Cl 1.1603-F-2-Cl 1.161 3-F-4-Cl 1.162 3-F-5-Cl 1.163 3-F-6-Cl 1.164 4-F-2-Cl1.165 4-F-3-Cl 1.166 2-Cl-4-Br 1.167 2-Cl-4-I 1.168 3-Cl-4-I 1.1694-Cl-2-Br 1.170 2-CN-3-F 1.171 2-CN-3-Cl 1.172 2-CN-4-Cl 1.173 2-CN-4-Br1.174 2-CN-4-NO₂ 1.175 4-CN-2-Cl 1.176 4-CN-2-CF₃ 1.177 4-CN-2-NO₂ 1.1782-NO₂-4-F 1.179 2-NO₂-4-Cl 1.180 2-NO₂-4-Br 1.181 2-NO₂-4-OCH₃ 1.1822-NO₂-4-OC₂H₅ 1.183 2-NO₂-5-Cl 1.184 3-NO₂-4-F 1.185 3-NO₂-4-Cl 1.1863-NO₂-4-Br 1.187 4-NO₂-2-Cl 1.188 4-NO₂-2-OCH₃ 1.189 5-NO₂-2-F 1.1905-NO₂-2-Cl 1.191 5-NO₂-2-Br 1.192 5-NO₂-2-OCH₃ 1.193 2-CH₃-4-F 1.1942-CH₃-4-Cl 1.195 2-CH₃-4-Br 1.196 2-CH₃-4-I 1.197 2-CH₃-4-NO₂ 1.1982-CH₃-4-OCH₃ 1.199 2-CH₃-3-F 1.200 2-CH₃-3-Cl 1.201 2-CH₃-3-NO₂ 1.2022-CH₃-5-F 1.203 2-CH₃-5-Cl 1.204 2-CH₃-5-Br 1.205 2-CH₃-5-NO₂ 1.2062-CH₃-6-Cl 1.207 2-CH3-6-C₂H₅ 1.208 2-CH₃-6-NO₂ 1.209 3-CH₃-2-Cl 1.2103-CH₃-2-Br 1.211 3-CH₃-4-Cl 1.212 3-CH₃-4-Br 1.213 3-CH₃-4-I 1.2144-CH₃-2-Cl 1.215 4-CH₃-3-Cl 1.216 4-CH₃-2-Br 1.217 4-CH₃-3-Br 1.2184-CH₃-3-F 1.219 4-CH₃-2-NO₂ 1.220 4-CH₃-3-NO₂ 1.221 5-CH₃-2-F 1.2225-CH₃-2-CN 1.223 5-CH₃-2-OCH₃ 1.224 4-C(CH₃)₃-2-Cl 1.225 2-CF₃-4-Cl1.226 2-CF₃-4-Br 1.227 2-CF₃-4-NO₂ 1.228 3-CF₃-4-F 1.229 3-CF₃-4-Cl1.230 3-CF₃-4-NO₂ 1.231 4-CF₃-2-Cl 1.232 4-CF₃-2-Br 1.233 4-CF₃-2-NO₂1.234 5-CF₃-2-Cl 1.235 5-CF₃-2-Br 1.236 5-CF₃-2-OCH₃ 1.237 2-OCH₃-5-Cl1.238 4-OCH₃-3-F 1.239 4-OCH₃-3-Cl 1.240 2-OCF₃-4-Cl 1.241 2-OCF₃-4-Br1.242 2-OCF₃-4-CN 1.243 4-OCF₃-2-Cl 1.244 4-OCF₃-2-Br 1.245 4-OCF₃-2-NO₂1.246 2-SCH₃-5-Cl 1.247 2,3,4-3F 1.248 2,3,4-3Cl 1.249 2,3,4-3Br 1.2502,3,5-3F 1.251 2,3,5-3Cl 1.252 2,3,5-3Br 1.253 2,3,6-3F 1.254 2,3,6-3Cl1.255 2,3,6-3Br 1.256 2,4,5-3F 1.257 2,4,5-3Cl 1.258 2,4,5-3Br 1.2592,4,6-3F 1.260 2,4,6-3Cl 1.261 2,4,6-3Br 1.262 3,4,5-3F 1.263 3,4,5-3Cl1.264 3,4,5-3Br 1.265 2,4,6-3CH₃ 1.266 2,4,6-3C₂H₅ 1.267 2,4,6-3CH(CH₃)₂1.268 2,4,6-3C(CH₃)₃ 1.269 2,4,6-3CF₃ 1.270 2,4,6-3NO₂ 1.271 2,4,6-3OCH₃1.272 3,4,5-3OCH₃ 1.273 2,4,6-3OCF₃ 1.274 2,4,6-3SCH₃ 1.275 2,4,6-3SCF₃1.276 2-F-4,6-2Br 1.277 2-F-4-Cl-6-Br 1.278 4-F-2,6-2Br 1.2792,4-2F-6-Cl 1.280 2,3-2Cl-4-Br 1.281 2-CH₃-4,6-2Br 1.282 3-CH₃-2,6-2Cl1.283 4-CH₃-2,6-2Br 1.284 2,3-2CH₃-6-NO₂ 1.285 4,5-2CH₃-2-NO₂ 1.2862,6-2CH₃-4-C(CH₃)₃ 1.287 2-CH₃-4-NO₂-6-Cl 1.288 2-CH₃-4-NO₂-6-Br 1.2892-CH₃-6-NO₂-4-Cl 1.290 2-CH₃-6-NO₂-4-Br 1.291 5-CH₃-4-F-6-Cl 1.2925-CH₃-2-OCH₃-4-Cl 1.293 2-CF₃-4,6-2Cl 1.294 2-CF₃-4,6-2Br 1.2954-CF₃-2,6-2Cl 1.296 4-CF₃-2,6-2Br 1.297 4-CF₃-2-NO₂-5-Cl 1.2984-CF₃-2-NO₂-6-Cl 1.299 4-CF₃-2-NO₂-6-Br 1.300 4-CF₃-2-Cl-6-Br 1.3012-NO₂-4,6-2Br 1.302 2-NO₂-4-F-5-Cl 1.303 4-NO₂-2,6-2Cl 1.3044-NO₂-2,6-2Br 1.305 4-NO₂-2,5-2Cl 1.306 2,4-2NO₂-6-Cl 1.3072,4-2NO₂-6-Br 1.308 2-CN-4,6-2Cl 1.309 2-CN-4,6-2Br 1.310 4-CN-2,6-2Cl1.311 2-CN-4-NO₂-6-Cl 1.312 2-CN-4-NO₂-6-Br 1.313 2,5-2OCH₃-4-NO₂ 1.3142,4-2OCH₃-5-Cl 1.315 2,3,5,6-4F 1.316 4-F-3-Cl-2,6-2Br 1.3176-NO₂-2,3,4-3F 1.318 2,3,4,5,6-5F 1.319 2,3,4,5,6-5Cl 1.3202,3,5,6-4F-4-CF₃ 1.321 H

Table 2: In the Formula I, when R₁═R₂═Br, R₃═heptafluoroisopropyl, X₁═F,X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a different substituentconsistent with table 1, successively corresponding to the substituentsrecorded in 1.1-1.321 of table 1; and the compounds are represented byNo. 2.1-2.321.

Table 3: In the Formula I, when R₁ ═R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 3.1-3.321.

Table 4: In the Formula I, when R₁═R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 4.1-4.321.

Table 5: In the Formula I, when R₁═CH₃, R₂═CH₂CH₃,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1, with the compounds are represented by No. 5.1-5.321.

Table 6: In the Formula I, when R₁═Br, R₂═CH₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 6.1-6.321.

Table 7: In the Formula I, when R₁═Br, R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 7.1-7.321.

Table 8: In the Formula I, when R₁═Br, R₂═I, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 8.1-8.321.

Table 9: In the Formula I, when R₁═Br, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 9.1-9.321.

Table 10: In the Formula I, when R₁═Cl, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 10.1-10.321.

Table 11: In the Formula I, when R₁═I, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 11.1-11.321.

Table 12: In the Formula I, when R₁═Br, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 12.1-12.321.

Table 13: In the Formula I, when R₁═Cl, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 13.1-13.321.

Table 14: In the Formula I, when R₁═I, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═H,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 14.1-14.321.

Table 15: In the Formula I, when R₁═R₂═CH₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 15.1-15.321.

Table 16: In the Formula I, when R₁═R₂═Br, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 16.1-16.321.

Table 17: In the Formula I, when R₁═R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 17.1-17.321.

Table 18: In the Formula I, when R₁═R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 18.1-18.321.

Table 19: In the Formula I, when R₁═CH₃, R₂═CH₂CH₃,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 19.1-19.321.

Table 20: In the Formula I, when R₁═Br, R₂═CH₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 20.1-20.321.

Table 21: In the Formula I, when R₁═Br, R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 21.1-21.321.

Table 22: In the Formula I, when R₁═Br, R₂═I, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 22.1-22.321.

Table 23: In the Formula I, when R₁═Br, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 23.1-23.321.

Table 24: In the Formula I, when R₁═Cl, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 24.1-24.321.

Table 25: In the Formula I, when R₁═I, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 25.1-25.321.

Table 26: In the Formula I, when R₁═Br, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 26.1-26.321.

Table 27: In the Formula I, when R₁═Cl, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 27.1-27.321.

Table 28: In the Formula I, when R₁═I, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═H and R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 28.1-28.321.

Table 29: In the Formula I, when R₁═R₂═CH₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 29.1-29.321.

Table 30: In the Formula I, when R₁═R₂═Br, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 30.1-30.321.

Table 31: In the Formula I, when R₁═R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 31.1-31.321.

Table 32: In the Formula I, when R₁═R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 32.1-32.321.

Table 33: In the Formula I, when R₁═CH₃, R₂═CH₂CH₃,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 33.1-33.321.

Table 34: In the Formula I, when R₁═Br, R₂═CH₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 34.1-34.321.

Table 35: In the Formula I, when R₁═Br, R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 35.1-35.321.

Table 36: In the Formula I, when R₁═Br, R₂═I, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 36.1-36.321.

Table 37: In the Formula I, when R₁═Br, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 37.1-37.321.

Table 38: In the Formula I, when R₁═Cl, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 38.1-38.321.

Table 39: In the Formula I, when R₁═I, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 39.1-39.321.

Table 40: In the Formula I, when R₁═Br, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 40.1-40.321.

Table 41: In the Formula I, when R₁═Cl, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 41.1-41.321.

Table 42: In the Formula I, when R₁═I, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═CH₃ and R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 42.1-42.321.

Table 43: In the Formula I, when R₁═R₂═CH₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 43.1-43.321.

Table 44: In the Formula I, when R₁═R₂═Br, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent as shown in table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1, and the compounds arerepresented by No. 44.1-44.321.

Table 45: In the Formula I, when R₁═R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 45.1-45.321.

Table 46: In the Formula I, when R₁═R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 46.1-46.321.

Table 47: In the Formula I, when R₁═CH₃, R₂═CH₂CH₃,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 47.1-47.321.

Table 48: In the Formula I, when R₁═Br, R₂═CH₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 48.1-48.321.

Table 49: In the Formula I, when R₁═Br, R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 49.1-49.321.

Table 50: In the Formula I, when R₁═Br, R₂═I, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent as shown in table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1, and the compounds arerepresented by No. 50.1-50.321.

Table 51: In the Formula I, when R₁═Br, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 51.1-51.321.

Table 52: In the Formula I, when R₁═Cl, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 52.1-52.321.

Table 53: In the Formula I, when R₁═I, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 53.1-53.321.

Table 54: In the Formula I, when R₁═Br, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 54.1-54.321.

Table 55: In the Formula I, when R₁═Cl, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 55.1-55.321.

Table 56: In the Formula I, when R₁═I, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H, R₄═cyanomethyl and R₅═CH₃,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 56.1-56.321.

Table 57: In the Formula I, when R₁═R₂═CH₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 57.1-57.321.

Table 58: In the Formula I, when R₁═R₂═Br, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 58.1-58.321.

Table 59: In the Formula I, when R₁═R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 59.1-59.321.

Table 60: In the Formula I, when R₁═R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 60.1-60.321.

Table 61: In the Formula I, when R₁═CH₃, R₂═CH₂CH₃,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 61.1-61.321.

Table 62: In the Formula I, when R₁═Br, R₂═CH₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 62.1-62.321.

Table 63: In the Formula I, when R₁═Br, R₂═Cl, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 63.1-63.321.

Table 64: In the Formula I, when R₁═Br, R₂═I, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 64.1-64.321.

Table 65: In the Formula I, when R₁═Br, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 65.1-65.321.

Table 66: In the Formula I, when R₁═Cl, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 66.1-66.321.

Table 67: In the Formula I, when R₁═I, R₂═CF₃, R₃═heptafluoroisopropyl,X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl, (R₆)_(n) is a differentsubstituent consistent with table 1, successively corresponding to thesubstituents recorded in 1.1-1.321 of table 1; and the compounds arerepresented by No. 67.1-67.321.

Table 68: In the Formula I, when R₁═Br, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 68.1-68.321.

Table 69: In the Formula I, when R₁═Cl, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 69.1-69.321.

Table 70: In the Formula I, when R₁═I, R₂═OCHF₂,R₃═heptafluoroisopropyl, X₁═F, X₂═X₃═X₄═H and R₄═R₅═cyanomethyl,(R₆)_(n) is a different substituent consistent with table 1,successively corresponding to the substituents recorded in 1.1-1.321 oftable 1; and the compounds are represented by No. 70.1-70.321.

The compound of the Formula I of the present invention can be preparedby the following method (in the Formula, unless otherwise specified, thedefinition of each group is the same as the above; and LG═Cl or Br):

A compound of Formula S and a compound of Formula K, or a compound ofFormula W and a compound of Formula Y react with each other in a propersolvent at the temperature from −10° C. to the boiling point of thesolvent for 0.5-48 h to prepare a compound of Formula II; and thereaction may be conducted in the presence of alkali.

The compound of Formula II reacts with haloacetonitrile in the presenceof a proper solvent and alkali at the temperature from −10° C. to theboiling point of the solvent for 0.5-48 h to respectively preparecompounds of Formulas I-1, I-2 and I-3. The compound of Formula 1 or 2reacts with haloacetonitrile in the presence of a proper solvent andalkali at the temperature from −10° C. to the boiling point of thesolvent for 0.5-48 h to prepare the compound of Formula I-3. Thecompound of Formula I-1 and a compound of Formula R₅-LG react with eachother in the presence of a proper solvent and alkali at the temperaturefrom −10° C. to the boiling point of the solvent for 0.5-48 h to preparea compound of Formula I-4. The compound of Formula I-2 reacts with acompound of R₄-LG in the presence of a proper solvent and alkali at thetemperature from −10° C. to the boiling point of the solvent for 0.5-48h to prepare a compound of Formula I-5. A compound of Formula III (R₅ ismerely a C₁-C₆ alkyl or C₁-C₆ haloalkyl) reacts with haloacetonitrile inthe presence of a proper solvent and alkali at the temperature from −10°C. to the boiling point of the solvent for 0.5-48 h to prepare thecompound of Formula I-4. A compound of Formula IV (R₄ is merely a C₁-C₆alkyl or C₁-C₆ haloalkyl) reacts with haloacetonitrile in the presenceof a proper solvent and alkali at the temperature from −10° C. to theboiling point of the solvent for 0.5-48 h to respectively prepare thecompound of Formula I-5.

The above proper solvent may be selected from aromatic hydrocarbons suchas benzene, methylbenzene and xylene, ketones such as acetone, methylethyl ketone and methyl isobutyl ketone, halohydrocarbons such aschloroform and dichloromethane, esters such as methyl acetate and ethylacetate, ethers such as tetrahydrofuran, dioxane, diethyl ether and1,2-dimethoxyethane, polar solvents such as water, acetonitrile, N,N-dimethylformamide, N-methyl pyrrolidone and dimethyl sulfoxide or amixture of the above solvents. The proper alkali may be selected fromorganic alkalis such as triethylamine, pyridine, DBU,4-dimethylamiopryidine, alkali metal hydrides such as sodium hydride andpotassium hydride, alkali metal hydroxides such as sodium hydroxide andpotassium hydroxide, alkali-earth metal hydroxides such as calciumhydroxide, alkali carbonate such as sodium carbonate and potassiumcarbonate, alkali metal bicarbonates such as sodium bicarbonate, andmetal alkoxides such as sodium methylate, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and sodium tert-butoxide.

The compounds of Formula R₄-LG Formula R₅-LG Formula K and FormulaCNCH₂-LG as well as alkali are usually commercially available, and alsomay be prepared according to a conventional method. The compounds ofFormula S, Formula W, Formula Y, Formula II, Formula III and Formula IVmay be prepared according to a common general method, for example,prepared according to the methods recorded in WO2011093415,US20110201687, WO2005021488, WO2005073165, WO2010018857, WO2006137395,JP2007099761, WO2008000438, WO2008074427, WO2008107091, WO2010013567,WO2010018714, WO2010090282, WO2010127926, WO2010127928, JP2011063549,WO2012020483, WO2012020484, WO2012077221, WO2012164698, WO2013050261,WO2014069665, WO2014067838, WO2014161848, WO2014161850, WO2015097091 orWO2015097094.

The compound of Formula I of the present invention has unexpectedly highinsecticidal activity, and can be used to control the following pests(the objects listed merely serve to specify the present invention, butare not to define the present invention): lepidoptera pests, such as,Plutella xylostella, armyworm, beet armyworm, prodenia litura, tobaccobudworm, cabbage looper, Chilo suppressalis, tryporyza incertulas, riceleaf roller, Ostrinia nubilalis, grapholtitha molesta busck, cottonbollworm; homopteran pests, such as, pea aphid, bean aphid, beet aphid,cotton aphid, apple aphid, green peach aphid, corn leaf aphid,aleyrodid, leafhopper, plant hopper, rice planthopper and mealybug;hemiptera pests, such as maize chinch bug, cotton lace bug, cyrtopeltismodesta distant, Nezara viridula and rice stink bug; thysanoptera pests,such as Thrips tabaci, frankliniella occidentalis and Thripsnigropilosus uzel; coleoptera pests, such as potato beetle, elateridae,clitea metallica chen, leaf miner and sympiezomias velatus chevrolat;diptera pests, such as flies and mosquitos; hymenoptera pests, such asbees and ants. The compound of Formula I of the present inventionfurther has unexpectedly high fast-acting insecticidal efficacy, andtakes effect rapidly; moreover, the compound of the Formula I canachieve higher insecticidal activity 1 day after application, andextremely high insecticidal activity within 3 days. The compound ofFormula I of the present invention has simple and efficient preparationmethod, facilitaets large-scale industrial production, and thus hasextensive application prospects. Therefore, the technical solution ofthe present invention further includes a use of the compound of theFormula I in the preparation of an insecticide in agriculture and otherfields.

Due to its positive property, the above compound can be advantageouslyused to protect important crops, livestock and breeding stock inagriculture and horticulture as well as the surroundings where peoplehaunt about from being damaged by the pests.

To achieve an ideal effect, the dosage of the above compound varies fromdifferent factors, for example, the compound used, crops to beprotected, type of pests, gradient of infection, weather conditions,application method, dosage forms taken, etc.

The compound at a dose of 10 g to 5 kg per hectare can take sufficientcontrol effect.

The present invention further includes an insecticidal composition withthe compound of Formula I as an active component. The weight percentageof the active component in the insecticidal composition is within0.1-99%. The insecticidal composition further includes a carrieracceptable in agriculture, forestry and health.

The composition of the present invention can be applied in the form offormulations. The compound of the Formula I, as an active component, isdissolved or dispersed into a carrier or formulated into formulations sothat it is easier to be dispersed when used as an insecticide. Forexample: these chemical formulations can be made into wettable powder,an oil suspension, a suspension concentrate, EW (emulsion in water), awater aqua or missible oil, etc. At least one kind of liquid or a solidcarrier is added to these compositions, and moreover, a propersurfactant may be added when needed.

The technical solution of the present invention further includes amethod for controlling pests: the insecticidal composition of thepresent invention is applied to the pests or a growth medium thereof.Usually, a more appropriately effective dose selected is from 10 g to1000 g per hectare; preferably, the effective dose is from 10 g to 500 gper hectare.

For some application, for example, one or more other bactericides,pesticides/acaricide, herbicides, plant growth regulators orfertilizers, etc. can be added to the insecticidal composition of thepresent invention in agriculture, thus bringing additional advantagesand effects.

It should be made clear that various transformations and alterations canbe made within the scope set forth in the claims of the presentinvention.

DETAILED DESCRIPTION OF THE INVENTION

The present invention is further described by the following detailedembodiments, but the present invention is not limited to these examples.(Unless otherwise specified, the raw materials used are commerciallyavailable)

EXAMPLES OF SYNTHESIS

The compound of Formula I of the present invention may be preparedrespectively with different raw materials based on the synthetic routedescribed above; and the further detailed description is as follows:

Example 1: Preparation of Compound 2.321

(1) Preparation of3-benzamido-N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide(intermediate II-1)

1.00 g (1.80 mmol)N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide(intermediate S-1, prepared by reference to the methods disclosed inWO2010013567, WO02010018714, US20110201687 or WO2011093415, etc.) and0.27 g (1.93 mmol) benzoyl chloride were added to 30 ml methylbenzene,and heating was performed for reflux. By TLC monitoring, and at the endof the reaction, the above solution was desolventized under reducedpressure; and then residuals were purified by column chromatography(eluent was ethyl acetate and petroleum ether with the volume ratio of1:6-1:2) to obtain 1.09 g white solid, namely, the intermediate II-1.

(2) Preparation of compound 2.321

0.30 g (7.5 mmol) 60% sodium hydride was added to 10 ml tetrahydrofuran,0.50 g (0.75 mmol)3-benzamido-N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide(intermediate II-1) dissolved in 10 ml tetrahydrofuran was dropped in atroom temperature, and then stirring was carried out for 10 min at roomtemperature; and 0.45 g (3.78 mmol) bromoacetonitrile was added andstirring was continued for 1 h at room temperature. By TLC monitoring,and at the end of the reaction, the reaction was quenched by ice water;ethyl acetate was added for extraction; an obtained product was dried byanhydrous magnesium sulfate, filtered, and desolventized under reducedpressure; and residuals were purified by column chromatography (eluentwas ethyl acetate and petroleum ether with the volume ratio of 1:6-1:2)to obtain 0.38 g white solid.

The nuclear magnetism and mass spectrometric data of the compound 2.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm): 8.10 (t,1H), 7.98 (d, 1H), 7.86 (s, 2H), 7.54-7.48(m, 1H), 7.41-7.29 (m, 4H),7.28-7.21(m, 2H), 4.80 (d, 2H).

¹H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.62 (d,1H), 8.04 (d, 2H), 7.66 (d, 2H), 7.44-7.27 (m, 6H), 4.93 (s, 2H).

LC-MS(m/z): 722.0 (m+Na+H).

Similarly, the compounds 2.7, 2.17 and 2.43 were prepared according tothe method of Example 1.

The nuclear magnetism and mass spectrometric data of the compound 2.7were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm): 8.13 (t,1H), 7.95 (d, 1H), 7.87 (s, 2H), 7.54-7.49 (m, 1H), 7.44-7.39 (m, 2H),7.35 (t, 1H), 6.95 (t, 2H), 4.79 (d, 2H).

¹H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.62 (s,1H), 8.04 (s, 2H), 7.73-7.65 (m, 2H), 7.48-7.42 (m, 2H), 7.38 (t, 1H),7.15 (t, 2H), 4.94 (s, 2H).

LC-MS(m/z): 718.1 (m+H).

The nuclear magnetism and mass spectrometric data of the compound 2.17were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm): 8.16 (t,1H), 7.88 (s, 2H), 7.57 (d, 2H), 7.53-7.48 (m, 3H), 7.37 (t, 1H), 7.34(s, 1H), 4.99 (s, 1H), 4.67 (s, 1H).

¹H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.59 (s,1H), 8.04 (s, 2H), 7.80 (d, 2H), 7.77-7.67 (m, 2H), 7.55 (d, 2H), 7.38(t, 1H), 4.99 (s, 2H).

LC-MS(m/z): 725.2 (m+H).

The nuclear magnetism and mass spectrometric data of the compound 2.43were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm):7.90-7.80 (m, 4H), 7.55 (d, 2H), 7.23 (s, 1H), 7.11 (s, 1H), 6.85 (s,1H), 4.39-4.31 (m, 1H), 4.08 (d, 2H).

LC-MS(m/z): 767.9 (m+H).

Example 2: Preparation of Compound 3.321

The method of preparing the compound 3.321 by 3-benzamido-N-(2,6-dichloro-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediateII-2, prepared by reference to the method disclosed in WO2010018857) isthe same as that of Example 1.

The nuclear magnetism and mass spectrometric data of the compound 3.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm): 8.10 (t,1H), 7.95 (d, 1H), 7.67 (s, 2H), 7.49 (t, 1H), 7.41-7.34 (m, 3H), 7.31(t, 1H), 7.29-7.22 (m, 2H), 4.80 (d, 2H).

¹H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.61 (s,1H), 7.92 (s, 2H), 7.70-7.58 (m, 2H), 7.42-7.27 (m, 6H), 4.93 (s, 2H).

LC-MS(m/z): 610.0 (m+H).

Example 3: Preparation of Compound 6.321

The method of preparing the compound 6.321 by3-benzamido-N-(2-bromo-6-methyl-4-heptafluoroisopropylphenyl)-2-fluorobenzamide(intermediate II-3, prepared by reference to the method disclosed inWO2010018857) is the same as that of Example 1.

The nuclear magnetism and mass spectrometric data of the compound 6.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm):8.12-8.06 (m, 1H), 7.90 (d, 1H), 7.72 (s, 1H), 7.51 (t, 1H), 7.51 (t,1H), 7.48 (s, 1H), 7.42-7.30 (m, 4H), 7.28-7.22 (m, 1H), 4.81 (d, 2H),2.38 (s, 3H).

¹H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.29 (s,1H), 7.80 (d, 1H), 7.70-7.64 (m, 2H), 7.59 (t, 1H), 7.38 (d, 3H),7.35-7.27 (m, 3H), 4.93 (s, 2H), 2.35 (s, 3H).

LC-MS(m/z): 634.0 (m+H).

Example 4: Preparation of Compound 7.321

The method of preparing the compound 7.321 by3-benzamido-N-(2-bromo-6-chloro-4-heptafluoroisopropylphenyl)-2-fluorobenzamide(intermediate II-4, prepared by reference to the method disclosed inWO2014161849) is the same as that of Example 1.

The nuclear magnetism and mass spectrometric data of the compound 7.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm): 8.10 (t,1H), 7.96 (d, 1H), 7.88-7.80 (m, 1H), 7.71 (d, 1H), 7.54-7.46 (m, 1H),7.42-7.29 (m, 4H), 7.28-7.21 (m, 2H), 4.80 (d, 2H).

¹H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.61 (s,1H), 8.05-7.99 (m, 1H), 7.95 (s, 1H), 7.71-7.58 (m, 2H), 7.42-7.27 (m,6H), 4.93 (s, 2H).

LC-MS(m/z): 654.0 (m+H).

Example 5: Preparation of Compound 8.321

The method of preparing the compound 8.321 by3-benzamido-N-(2-bromo-6-iodo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide(intermediate II-5, prepared by reference to the method disclosed inWO2010018857) is the same as that of Example 1.

The nuclear magnetism and mass spectrometric data of the compound 8.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm): 8.12 (t,1H), 8.06 (d, 1H), 7.96 (d, 1H), 7.89 (d, 1H), 7.54 (t, 1H), 7.42-7.31(m, 4H), 7.28-7.21 (m, 2H), 4.81 (d, 2H).

¹H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.61 (s,1H), 8.14 (s, 1H), 8.02 (s, 1H), 7.70 (t, 1H), 7.66-7.60 (m, 1H),7.41-7.28 (m, 6H), 4.93 (s, 2H).

LC-MS(m/z): 745.9 (m+H).

Example 6: Preparation of Compound 9.321

The method of preparing the compound 9.321 by3-benzamido-N-(2-bromo-6-trifluoromethyl-4-heptafluoroisopropylphenyl)-2-fluorobenzamide(intermediate II-6, prepared by reference to the methods disclosed inWO2010013567, WO2010018714, US20110201687 or WO2011093415, etc.) is thesame as that of Example 1.

The nuclear magnetism and mass spectrometric data of the compound 9.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm): 8.13 (s,1H), 8.08 (t, 1H), 8.03 (d, 1H), 7.91 (s, 1H), 7.53 (t, 1H), 7.40-7.30(m, 4H), 7.28-7.22 (m, 2H), 4.80 (d, 2H).

¹H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.66 (s,1H), 8.40 (d, 1H), 7.94 (d, 1H), 7.62 (q, 2H), 7.39-7.31 (m, 4H), 7.28(t, 2H), 4.91 (s, 2H).

LC-MS(m/z): 687.9 (m+H).

Example 7: Preparation of Compound 16.321

0.5 g (0.75 mmol)3-benzamido-N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide(intermediate II-1), 0.18 g (1.51 mmol) bromoacetonitrile, and 0.17 g(1.52 mmol) potassium tert-butoxide were added to 20 ml tetrahydrofuran,and then stirred for 5 h at room temperature. By TLC monitoring, and atthe end of the reaction, water and ethyl acetate were added forextraction; an obtained product was dried by anhydrous magnesiumsulfate, filtered, and desolventized under reduced pressure; residualswere purified by column chromatography (eluent was ethyl acetate andpetroleum ether with the volume ratio of 1:6-1:2) to obtain 0.29 g whitesolid.

The nuclear magnetism and mass spectrometric data of the compound 16.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm): 8.52(td, 1H), 8.08 (s, 1H), 7.88-7.83 (m, 2H), 7.79 (s, 2H), 7.62-7.57 (m,1H), 7.54-7.50 (m, 2H), 6.98-6.93 (m, 1H), 6.92-6.88 (m, 1H), 4.72 (s,2H). LC-MS(m/z): 699.9 (m+H).

Similarly, the compounds 17.321, 20.321 and 21.321 were preparedaccording to the method of Example 7.

The nuclear magnetism and mass spectrometric data of the compound 17.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm):8.54-8.48 (m, 1H), 8.04 (d, 1H), 7.87-7.82 (m, 2H), 7.60-7.57 (m, 3H),7.54-7.50 (m, 2H), 6.97 (t, 1H), 6.92-6.87 (m, 1H), 4.74 (s, 2H).LC-MS(m/z): 610.0 (m+H).

The nuclear magnetism and mass spectrometric data of the compound 20.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm):8.51-8.45 (m, 1H), 8.00 (d, 1H), 7.87-7.82 (m, 2H), 7.71 (s, 1H),7.62-7.58 (m, 1H), 7.54-7.50 (m, 2H), 7.37 (s, 1H), 6.97 (t, 1H),6.93-6.89 (m, 1H), 5.14 (d, 1H), 4.35 (d, 1H), 2.43 (s, 3H). LC-MS(m/z):634.0 (m+H).

The nuclear magnetism and mass spectrometric data of the compound 21.321were as follows: ¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃)δ (ppm): 8.56-8.50 (m, 1H), 8.05 (s, 1H), 7.88-7.83 (m, 2H), 7.76 (d,1H), 7.64-7.58 (m, 2H), 7.56-7.50 (m, 2H), 6.97 (t, 1H), 6.93-6.87 (m,1H), 4.79 (d, 1H), 4.68 (d, 1H). LC-MS(m/z): 654.0 (m+H).

Example 8: Preparation of Compound 30.321

0.5 g (0.74 mmol)N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-(N-benzamido)benzamide (intermediate IV-1, prepared by reference to the methodsdisclosed in WO2010013567, WO2010018714, US20110201687 or WO2011093415,etc.), 0.18 g (1.51 mmol) bromoacetonitrile and 0.17 g (1.52 mmol)potassium tert-butoxide were added to 20 ml DMF, and then stirred atroom temperature for 10 h. By TLC monitoring, and at the end of thereaction, water and ethyl acetate were added for extraction; an obtainedproduct was dried by anhydrous magnesium sulfate, filtered, anddesolventized under reduced pressure; and residuals were purified bycolumn chromatography (eluent was ethyl acetate and petroleum ether withthe volume ratio of 1:6-1:2) to obtain 0.34 g white solid.

The nuclear magnetism and mass spectrometric data of the compound 30.321were as follows:

¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃) δ (ppm): 7.76 (s,2H), 7.49-7.37 (m, 1H), 7.28-7.21 (m, 2H), 7.18-7.10 (m, 3H), 7.00-6.94(m, 1H), 6.80-6.74 (m, 1H), 4.69(s, 2H), 3.27 (s, 3H).

¹H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 7.99 (s,2H), 7.31-7.25(m, 2H), 7.24-7.16 (m, 4H), 7.07-7.01 (m, 1H), 6.94-6.88(m, 1H), 4.88 (s, 2H), 3.18 (s, 3H).

LC-MS(m/z): 713.9 (m+H).

Example 9: Preparation of Compound 58.321

0.5 g (0.75 mmol)3-benzamido-N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide(intermediate II-1), 0.45 g (3.78 mmol) bromoacetonitrile and 0.42 g(3.75 mmol) potassium tert-butoxide were added to 20 ml tetrahydrofuran,and then stirred at room temperature for 5 h. By TLC monitoring, and atthe end of the reaction, water and ethyl acetate were added forextraction; an obtained product was dried by anhydrous magnesiumsulfate, filtered, and desolventized under reduced pressure; andresiduals were purified by column chromatography (eluent was ethylacetate and petroleum ether with the volume ratio of 1:6-1:2) to obtain0.26 g white solid.

The nuclear magnetism and mass spectrometric data of the compound 58.321were as follows: ¹H NMR (600 MHz, internal standard TMS, solvent CDCl₃)δ (ppm): 7.77 (s, 2H), 7.33-7.28 (m, 3H), 7.18 (t, 2H), 7.16-7.12 (m,1H), 7.09 (t, 1H), 6.82 (t, 1H), 5.05 (s, 1H), 4.69 (d, 2H), 4.20 (s,1H). LC-MS(m/z): 760.9 (m+H).

Other compounds of Formula I of the present invention can be prepared byreference to the above Examples.

Determination of Biological Activity

Example 10: Determination of Insecticidal Activity

Experiments for the determination of the insecticidal activity of thecompound against several kinds of pests were carried out. Adetermination method was as follows.

The compound to be tested was dissolved by a mixed solvent ofacetone/methanol (1:1), and then diluted by water containing 0.1% (wt)Tween 80 to the required concentration.

An Airbrush spray method was adopted for the determination of theactivity, with armyworm, Plutella xylostella and Chilo suppressalis astargets.

(1) Determination of insecticidal activity against armyworm

Determination method: maize blades were cut into 2 cm (length) segments;with the pressure of Airbrush spray being 10 psi (about 0.7 kg/cm²),both sides of each blade segment were sprayed with the amount of 0.5 ml.After dried in the shade, each segment was inoculated with 10 3rd-instarlarvaes, 3 repeats for each segment. And then, the treated segments wereput into an observation room (25° C., relative humidity: 60-70%) forcultivation; the number of the survivals was surveyed 1 d, 2 d and 3 dafter administration, and then the death rate was calculated.

Partial test results with regard to armyworm were as follows:

the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 6.321,7.321, 8.321, 9.321, 16.321, 17.321, 20.321, 21.321, 30.321 and 58.321against armyworm was 90% or more at a dose of 0.5 mg/L, 3 d afteradministration;

the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 7.321,8.321, 9.321, 16.321, 17.321, 21.321, 30.321 and 58.321 against armywormwas 90% ore more at a dose of 0.1 mg/L, 3 d after administration;

the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 9.321 and 30.321against armyworm was 90% or more at a dose of 0.05 mg/L, 3 d afteradministration;

(2) Determination of insecticidal activity against Plutella xylostella

Determination method: cabbage blades were punched into 2 cm (diameter)leaf discs by a puncher; with the pressure of Airbrush spray being 10psi (about 0.7 kg/cm²), both sides of each leaf disc were sprayed withthe amount of 0.5 ml. After dried in the shade, each leaf disc wasinoculated with 10 3rd-instar larvaes, 3 repeats for each leaf disc. Andthen, the treated leaf discs were put into an observation room (25° C.,relative humidity: 60-70%) for cultivation; the number of the survivalswas surveyed 1 d, 2 d and 3 d after administration, and then the deathrate was calculated.

Partial test results with regard to Plutella xylostella were as follows:

the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 6.321,7.321, 8.321, 9.321, 16.321, 17.321, 20.321, 21.321, 30.321, and 58.321against Plutella xylostella was 90% or more at a dose of 1 mg/L, 3 dafter administration;

the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 9.321, 16.321,30.321, and 58.321 against Plutella xylostella was 90% or more at a doseof 0.5 mg/L, 3 d after administration.

The fatality rate of compounds 9.321 and 30.321 against Plutellaxylostella was 90% or more at a dose of 0.05 mg/L, 3 d afteradministration.

CK1, CK2, CK3 and CK4 were selected as control compounds, and compounds2.7, 2.17, 2.43, 2.321, 3.321, 6.321, 7.321, 8.321, 9.321, 16.321,17.321, 20.321, 21.321, 30.321 and 58.321 in the present invention wereselected for a parallel comparison test for the insecticidal activityagainst Plutella xylostella (3 d after administration); thedetermination method was the same as described above; and the resultswere shown in table 71:

TABLE 71 Parallel comparison test for the insecticidal activity ofpartial compounds of the present invention and CK1-CK4 against plutellaxylostella Fatality rate (%, 3 d after administration) Compound No. 10mg/L 2.7 100 2.17 100 2.43 100 2.321 100 3.321 100 6.321 100 7.321 1008.321 100 9.321 100 16.321 100 17.321 100 20.321 100 21.321 100 30.321100 58.321 100 CK1 0 CK2 0 CK3 0 CK4 0

CK5, CK8 and CK12 were selected as control compounds, and compounds6.321 and 20.321 in the present invention were selected for a parallelcomparison test for the insecticidal activity against Plutellaxylostella (3 d after administration); the determination method was thesame as described above; and the results were shown in table 72:

TABLE 72 Parallel comparison test for the insecticidal activity ofcompounds 6.321 and 20.321 of the present invention and CK5, CK8, andCK12 against plutella xylostella Fatality rate (%, 3 d afteradministration) Compound No. 5 mg/L 1 mg/L  6.321 100 98.5 20.321 10093.9 CK5 63.5 0 CK8 65.8 0  CK12 60 0

CK6, CK9, CK10, CK13 and CK15 were selected as control compounds, andcompounds 2.7, 2.17, 2.43, 2.321, 16.321, 30.321 and 58.321 in thepresent invention were selected for a parallel comparison test for theinsecticidal activity against Plutella xylostella (3 d afteradministration); the determination method was the same as describedabove; and the results were shown in table 73:

TABLE 73 Parallel comparison test for the insecticidal activity ofpartial compounds of the present invention and CK6, CK9, CK10, CK13 andCK15 against plutella xylostella Fatality rate (%, 3 d afteradministration) Compound No. 1 mg/L 0.5 mg/L 2.7 100 100 2.17 100 1002.43 100 100 2.321 100 100 16.321 100 100 30.321 100 100 58.321 100 98CK6  68 10 CK9  55 0 CK10 55 0 CK13 75 0 CK15 90 50

CK7, CK11, CK14 and CK16 were selected as control compounds, andcompounds 9.321 and 30.321 in the present invention were selected for aparallel comparison test for the insecticidal activity against Plutellaxylostella (3 d after administration); the determination method was thesame as the above; and the results were shown in table 74:

TABLE 74 Parallel comparison test for the insecticidal activity ofcompounds 9.321 and 30.321 of the present invention and CK7, CK11 CK14,CK16 against plutella xylostella Fatality rate (%, 3 d afteradministration) Compound No. 0.5 mg/L 0.05 mg/L  9.321 100 100 30.321100 100 CK7  70 0 CK11 75 0 CK14 60 0 CK16 100 80.8

CK15 was selected as a control compound, and compounds 2.321 and 30.321in the present invention were selected for a parallel comparison testfor the insecticidal activity against Plutella xylostella, so as tocompare the fast-acting insecticidal efficacy; and the results wereshown in table 75:

TABLE 75 Comparison test for the fast-acting insecticidal efficacy ofcompounds 2.321 and 30.321 of the present invention and CK15 againstplutella xylostella Fatality rate (%) Compound Dose 1 d after 2 d after3 d after No. (mg/L) administration administration administration  2.3210.5 80 95 100 30.321 0.5 90 100 100 CK15 0.5 0 30 50

It can be seen from table 75 that compared with the existing compoundCK15, the compound of the present invention has more excellentfast-acting insecticidal efficacy and higher insecticidal activity at alower dose.

CK16 was selected as a control compound, and compound 9.321 in thepresent invention was selected for a parallel comparison test for theinsecticidal activity against Plutella xylostella, so as to compare thefast-acting insecticidal efficacy; and the results were shown in table76:

TABLE 76 Comparison test for the fast-acting insecticidal efficacy ofcompound 9.321 of the present invention and CK16 against plutellaxylostella Fatality rate (%) Compound Dose 1 d after 2 d after 3 d afterNo. (mg/L) administration administration administration 9.321 0.05 70 95100 CK16 0.05 0 52.5 80.8

It can be seen from table 76 that compared with the existing compoundCK16, the compound of the present invention has more excellentfast-acting insecticidal efficacy and higher insecticidal activity at alower dose.

(3) Determination of insecticidal activity against Chilo suppressalis

Determination method: 1) preparation of rice seedlings: rice wascultivated in small plastic cups (diameter: 4.5 cm and height: 4 cm) ata constant temperature room (temperature: 26-28° C., relative humidity:60-80% around and illumination: 16 hL:8 hD), after the rice grew to a4-5 leaf stage, vigorous and uniform-growth rice seedlings were selectedand treated with an insecticide, 3 repeats for each treatment. 2)Preparation of pests for test: 3rd-instar larvaes of Chilo suppressalisfed continuously in the room. 3) Inoculation of pests on rice stems byspray. The whole plants of the rice seedlings were sprayed by a spraymethod uniformly, with the dose of 15 ml for each treatment. The blankcontrol was treated first, and the above operation was repeated in anorder of lower to higher test concentration. After sprayed, riceseedlings were placed in the shade to dry the insecticide liquor, andthen stalks about 5 cm above the basal part of the stems were cut to befed to the pests for test. Glass petri dishes (diameter: 9 mm) wereprepared, cushioned by filter paper at the bottom thereof, and subjectedto water addition for moisturizing; about 20 pieces of rice stems wereput in each dish and inoculated with 10 larvaes; then the petri disheswere closed by non-woven fabrics and placed in a constant temperatureroom for culture. The number of survivals was surveyed 3 d afteradministration.

Partial test results with regard to Chilo suppressalis were as follows:

the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 6.321,7.321, 8.321, 9.321, 16.321, 17.321, 20.321, 21.321, 30.321 and 58.321against Chilo suppressalis was 90% or more at a dose of 40 mg/L;

the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 7.321,8.321, 9.321, 16.321, 17.321, 21.321, 30.321 and 58.321 against Chilosuppressalis was 90% or more at a dose of 4 mg/L; the fatality rate ofcompounds 2.7, 2.17, 2.43, 2.321, 9.321 and 30.321 against Chilosuppressalis was 90% or more at a dose of 1 mg/L.

CK15 was selected as a control compound, and compounds 2.321 and 30.321in the present invention were selected for a parallel comparison testfor the insecticidal activity against Chilo suppressalis; thedetermination method was the same as described above; and the resultswere shown in table 77:

TABLE 77 Comparison of the insecticidal activity against chilosuppressalis between each of the compounds 2.321 and 30.321 in thepresent invention and CK15 Fatality rate (%, 3 d after administration)Compound No. 5 mg/L 2.5 mg/L 1.25 mg/L  2.321 100 100 95.5 30.321 100100 93.5 CK15 50.3 22.2 8.6

It can be seen from table 77 that compared with the existing compoundCK15, the compound of the present invention has the advantage ofexerting better insecticidal efficacy at a lower dose. CK16 was selectedas a control compound, and compound 9.321 in the present invention wasselected for a parallel comparison test for the insecticidal activityagainst Chilo suppressalis; the determination method was the same asdescribed above; and the results were shown in table 78:

TABLE 78 Comparison of the insecticidal activity against chilosuppressalis between compound 9.321 in the present invention and CK16Fatality rate (%, 3 d after administration) Compound No. 2.5 mg/L 1.25mg/L 0.625 mg/L 9.321 100 100 98 CK16 85.5 60.3 10

It can be seen from table 78 that compared with the existing compoundCK16, the compound of the present invention has the advantage ofexerting better insecticidal efficacy at a lower dose. The inventor ofthe present invention introduces a cyanomethyl (CNCH₂—) properly on theN atom of its amido bond on the basis of the molecular skeleton of theexisting compound, thus obtaining the compound of Formula I of thepresent invention. It can be seen from data of the comparison tests oftables 71-78 that the introduction of a new proper segment (an efficacygroup) increases the opportunity of a molecule to interact and bond witha receptor; therefore, the compound of the present invention hasunexpected effect relative to the existing compounds. That is, thecompound of the present invention has higher insecticidal activity andmore excellent fast-acting insecticidal efficacy (the compound of thepresent invention takes effect rapidly, and can achieve higherinsecticidal activity 1 d after application, and extremely highinsecticidal activity within 3 d).

In organic molecules, due to the difference of substituents inelectronegativity, volume or steric configuration, there is a markedvariation in conductivity or receptor binding capacity of the wholemolecule in biological bodies, such as insects and plants, andaccordingly, the molecule shows obvious difference in biologicalactivity. Moreover, the conductivity or receptor binding appropriatenessof the molecule cannot be expected, and can be obtained in need of alarge amount of creative efforts. Therefore, the present inventionpossesses substantive features and significant progress.

The invention claimed is:
 1. A benzamide compound, as shown in FormulaI:

in the formula: R₁ and R₂ are each independently selected from H,halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy;R₃ is selected from heptafluoroisopropyl or nonafluoro-2-butyl; R₄ andR₅ are each independently selected from H, C₁-C₆ alkyl, C₁-C₆ haloalkylor cyanomethyl; moreover, at least one of R₄ and R₅ is selected fromcyanomethyl; R₆ is selected from H, halogen, cyano, nitryl, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy; C₁-C₆ alkylthio orC₁-C₆ haloalkylthio; n=1, 2, 3, 4 or 5; X₁, X₂, X₃, and X₄ are eachindependently selected from H, halogen, cyano or C₁-C₆ alkoxy; and, X₁,X₂, X₃, and X₄ are not simultaneously H.
 2. The compound according toclaim 1, wherein, in the Formula I, R₁ and R₂ are each independentlyselected from H, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy orC₁-C₄ haloalkoxy; R₃ is selected from heptafluoroisopropyl ornonafluoro-2-butyl; R₄ and R₅ are each independently selected from H,methyl, ethyl or cyanomethyl; moreover, at least one of R₄ and R₅ isselected from cyanomethyl; R₆ is selected from H, halogen, cyano,nitryl, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy;C₁-C₄ alkylthio or C₁-C₄ haloalkylthio; n=1, 2, 3, or 4; X₁ is selectedfrom F; X₂, X₃, and X₄ are each independently selected from H, F orcyano.
 3. The compound according to claim 2, wherein, in the Formula I,R₁ and R₂ are each independently selected from H, halogen, methyl,ethyl, trifluoromethyl or difluoromethoxy; R₃ is selected fromheptafluoroisopropyl or nonafluoro-2-butyl; R₄ and R₅ are eachindependently selected from H, methyl, ethyl or cyanomethyl; moreover,at least one of R₄ and R₅ is selected from cyanomethyl; R₆ is selectedfrom H, F, Cl, Br, cyano, nitryl, methyl, ethyl, propyl, tertiary butyl,trifluoromethyl, heptafluoroisopropyl, methoxy or trifluoromethoxy; n=1,2 or 3; X₁ is selected from F; X₂, X₃, and X₄ are each independentlyselected from H, or F.
 4. The compound according to claim 1, wherein, inthe Formula I, R₁ and R₂ are each independently selected from H,halogen, methyl, ethyl, trifluoromethyl or difluoromethoxy; R₃ isselected from heptafluoroisopropyl or nonafluoro-2-butyl; R₄ is selectedfrom cyanomethyl; R₅ is selected from H, methyl, ethyl or cyanomethyl;R₆ is selected from H, F, Cl, Br, cyano, nitryl, methyl, ethyl, propyl,tertiary butyl, trifluoromethyl, heptafluoroisopropyl, methoxy ortrifluoromethoxy; n=1, 2 or 3; X₁ is selected from F; X₂, X₃, and X₄ areeach independently selected from H, or F.
 5. The compound according toclaim 1, wherein, in the Formula I, R₁ and R₂ are each independentlyselected from H, halogen, methyl, ethyl, trifluoromethyl ordifluoromethoxy; R₃ is selected from heptafluoroisopropyl ornonafluoro-2-butyl; R₄ is selected from H, methyl, or ethyl; R₅ isselected from cyanomethyl; R₆ is selected from H, F, Cl, Br, cyano,nitryl, methyl, ethyl, propyl, tertiary butyl, trifluoromethyl,heptafluoroisopropyl, methoxy or trifluoromethoxy; n=1, 2 or 3; X₁ isselected from F; X₂, X₃, and X₄ are each independently selected from H,or F.
 6. An insecticidal composition, wherein the composition comprisesthe compound of Formula I according to claim 1 as an active component;the percentage by weight of the active component in the composition iswithin 0.1-99%.
 7. A method of controlling pests in agriculture andforestry, wherein an effective amount of the composition according toclaim 6 is applied to a pest to be controlled or onto a growth mediumthereof.